I'm writing a story series, actually have been posting to gurochan for a few weeks but seems like it fits better here. Anyway, I will be updating regularly and would love to get feedback/comments.

Chapter 1: The Sleepover

“So how was your first date with Jason, Steph?” Anna asked her best friend.

“Yeah, did he make any moves on you?” Valerie added.

The three best friends were at Stephanie’s house for a sleepover, a tradition the girls tried to keep up at least once a month. Anna and Stephanie had been friends since elementary school, even though Anna was a year younger. Valerie became the third member of their group when she moved into Anna’s class 7th grade class last year. Even though Stephanie had graduated to high school, they still saw each other in the halls plenty since the middle and high schools occupied the same building.

“No. Well, we made out a bit during the movie. But after we went to his friend’s house to hang out like usual.”

Stephanie had a crush on the upper class boy since last October, and had been hanging out with his group of friends dropping hints all winter. She didn’t think she had a chance compared to the upper class girls, she was still in an awkward stage of puberty where those girls were all very developed. She stood head and shoulders taller than her two friends at 5’7”, but was still a little stocky with small A-cup breasts, and an ass she thought was too big. He had surprised her when he asked her to Prom, still months away, and was very nervous.

“I don’t know if he wanted more, we went back to his friend’s house after and hung out with the usual crowd.” Stephanie said, and Anna picked up on her tone.

“Oh fuck those other bitches, I keep telling you you’re just as hot as they are!” Anna slapped Steph’s ass playfully. “I bet none of them have got an ass half as good as yours!”

“Oh quit it, it’s easy for you to say everybody would drool over you!” She wasn’t wrong. Puberty had already blessed Anna with a very nice body, despite her being the youngest of the three. In fact, if it weren’t for her tiny 4’9”, 85 lb frame, you’d guess she was the oldest. She had very perky C-cup breasts, which looked massive on her body, a very slender waist that curved into generous hips and a butt that, while smaller than Steph’s, filled out a pair of pants very well. He legs were long, well long for her body, and she loved to show them off. He face still had a little baby fat to show her young age, but she framed it with light blonde hair she kept long, reaching halfway down her back. If it weren’t for her short stature she would certainly be classified as a ‘blonde bombshell.’

“Oh, you both need to quit bitching! Everybody still thinks I’m a little girl!” Valerie was understandably upset. It seems puberty hadn’t yet reached her. She stood taller than Anna, 5’ 1”, but other than that looked every bit younger. She was still flat chested, with straight hips and not much of an ass to brag about. It was something that often bothered her about her appearance, especially going through middle school watching the other girls grow into their bodies.

Steph’s phone buzzed as she received a text from Jason. She typed a response out and put it down.

“What did he want?” Valerie leaned over to the phone, curious.

“Just said what’s up, I told him we’re having a sleepover.” Steph didn’t seem interested in texting with him, but Valerie took the phone as it buzzed again.
“’Sounds hot, what are you wearing?’ Ooo, someone’s fishing for some pics!” Anna teased Steph.

“You were worried about those other girls, now’s the time to show off!” Valerie encouraged her. “We just gotta make you look real hot.”

It would take a little work, she wasn’t actually wearing lingerie. Her pajamas were a nice silk set though, loose shorts and a button up top. Anna and Valerie went to work. The shorts were rolled up, sides tucked into the waistband to create a makeshift thong. It looked a little odd, but did show her ass off spectacularly. Anna unbuttoned Steph’s shirt so it hung a little open, just teasing a look at her small breasts.

“There, I think that’s good.” The girls stepped back to assess their work.
“Ok, now give me a sexy pose. Stick out your ass a bit, and turn around so we can see inside your shirt.” Anna directed Steph.

“I don’t know you guys, I don’t know if this is a good idea.” Steph was still blushing, and having second thoughts.

“C’mon, we won’t show anything and its just one little pic! And you gotta get Jason excited, keep him interested.” Valerie pushed Steph.

“Well, ok, but just one ok?” Steph tried her best to hid her blush, and made seductive looks at the phone. Valerie took a couple pictures, decided on one and sent it.

After sending the racy pictures of Steph to Jason, the girls giggled for awhile and waited for a response.
*ding*

“Oh oh oh what did he say?!” Valerie looked down at the phone. Steph was bright red.

“Gimme that!” With the phone in reach now, Steph snatched it back from Anna. It buzzed a few more times, but she wouldn’t give it up this time.

“Oh god. Phill is there too apparently.”

“Ooo, the boy who was asking about Anna?” Valerie perked up, excited by the new development.

“Yeah, and thanks to you assholes now he’s seen my ass too! Wait, now he’s asking for your number, Anna.”

“I don’t know you guys. Why’d you tell him I’m here?!”

“Too late, I gave him your number!” Steph laughed.
Anna’s phone lit up near her bag, and this time Valerie got to it first.

“’Hey sexy, looks like you’re having a fun sleep over.’ I’m guessing this is the mysterious Phill.”

“Oh, we should send him a sexy pic too! You guys made me do it, and Anna doesn’t even need to change to look slutty!”

“Oh fuck you.” It was true though. Steph’s silky pajama shorts and top took some work and clever changes to show off some skin, and Val was in plain pajama pants with a baggy t shirt. Anna on the other hand was wearing a sheer negligee that ended a couple inches from her ass, and only then because of her tiny frame. It had a built in bra which pushed her breasts, already a sizeable C cup for her age, up and showed them off very generous cleavage. The loose fabric of the dress portion was sheer enough to show off her, flat stomach and tiny waist that curved out into full hips with a sizable ass. Her underwear left very little to the imagination as well, Anna had replaced all of her childhood panties with almost exclusively thongs last year, and the one she had on now was a black lace g string which could only obscure her already wet vagina.

“Oh c’mon Anna, I did it!” Steph cajoled her. Valerie still had Anna’s phone, so she snapped a picture of her sitting on the bed. Even though she wasn’t posing for it, you could still see all the way up her legs to the gentle curve of her ass as she sat there.

“Hey!” Anna tried to grab the phone, but Val was ready and Anna was too slow. “Fine, but don’t send that! At least let me try to take a good one.”

Anna brushed her long blonde hair back, giving better view of her ample cleavage. She sat up on her knees, then leaned forward towards Val, using her arms to push her breasts out more as she got on all fours.
“How’s this?” Anna gave her best seductive look to the camera.

“He’s going to lose his mind!” Valerie started taking some pictures. After she took a few, Steph chimed in.

“Enough of your tits, why not show off that cute little ass of yours Anna?” Steph pointed to the vanity in her room. “Go stand against that, give him a good look!”

Anna was getting into it now, it was all in good fun she thought. All three were getting into it, trying to best show off Anna’s figure for the camera, and she was having fun modeling. She leaned against the table of the vanity, looking over her shoulder as the hem of her nightie creeped higher and higher on her ass, showing off fully half of it.

“Got some good ones, Val?”

“Oh yeah, I would say so!” Valerie was smiling ear to ear.

Anna slowly slid each spaghetti strap off her shoulders, and let the dress fall off her body. Now totally naked except for a tiny thong, put one arm across her chest, succeeding in only really covering her nipples with her skinny arm.

“Now this is how you do it.” She said, and Val took some pictures while she tried her best stripper moves and Steph cheered her on laughing.
After taking a few pictures, Anna pulled her lingerie back on a walked tolds Valerie. “Ok, lemme see what you got.”

Valerie and Steph both started backing away, giggling as they failed to hold back their laughter. Anna’s face changed to concern. “What did you do, gimme the phone!”

Valerie let her grab it, and both girls burst into giggles and jumped on the bed. Anna looked at the phone and her heart skipped more than a few beats. There on the screen was an open text conversation, with Phill. There were more than a few pictures sent, and the last was her leaned on the vanity, turning back towards the camera with one of her tits fully on display. Under that, one reply: Holy fuck.

“AAAHHH!!!” Anna screamed and leapt at her friends on the bed. Several minutes of furious clawing, punching and wrestling later the three tired themselves out.

“God, you can see my nipple full on in this one!” Anna was looking through the pictures Val sent. “I was going to look through them and send the good ones!”

“Well, where’s the fun in that?” Val said.

“And you know what? Not just Phill saw it, I’m sure Jason did too! How’s that for payback!” Steph looked pleased with herself.

“Oh fuck…” the situation was dawning on Anna now.

“You know, I just sent sexy pics to Jason, but you were totally naked in those Anna! That’s porn!”

“You’re a child pornstar now Anna!” Valerie teased.

“Shush, he texted back! He wants to go out with me, what do I say?”

“Say yes, DUH!” Both girls answered.

“Oh and we’ve been giving them plenty, he should send us a sexy pic too! It’s only fair.” Valerie prodded Anna.

“Ok, I told him I’d go with him to the movies but only if he sends us something hot enough.” Valerie and Steph took positions over Anna’s shoulders waiting for the reply to come on her phone. When it came a minute late, all three were dumbstruck.
Steph was the first to recover.“Holy fuck that can’t be real.”

What Phill texted back was simply a down angled shot of his naked lap, with his erect cock in his hand. The massive member dominated the screen, and it looked like he could barely fit his hand around it.

“Well I think that settles it, Anna. You’re going on a date with Phill, and from the looks of it you’ll have your hands full.”

Later that night, they had all gone to bed after more gossip and giggles. Steph and Val were sharing Steph’s bed, while Anna was in her sleeping bag on the floor. The others were sound asleep, but Anna couldn’t seem to fall asleep. Now that it was quiet, she keep her mind from drifting back to the picture she had on her phone. Finally, she carefully made sure her friends were asleep, then opened her laptop up and put her headphones on.

Anna opened one of her favorite porn sites, and clicked the first link that looked interesting. A young blonde woman with huge, obviously fake tits was being fucked from behind while a second man used her mouth. Anna tried to imagine herself there, bit her lower lip as she thought of that man grabbing her by the hips, slamming her back onto his cock. The woman was gagging as the man in front began fucking her throat harder and harder. Anna’s hand wandered from the mouse to her own throat, wondering what it felt like to have a cock push its way down it. Her fingers worked her clit harder as she imagined choking on a cock, tightening her grip around her throat. This was getting her close, but it was too tame for her standards.

Teen begs for mercy during rough gangbang.

This was it. When it first started, Anna thought she would be disappointed by another clickbait exaggerated title. It opened like many others, with a pretty girl wearing too much make up on her knees in front of two men. She was naked and one of the men, a tall severe looking muscular man, was holding her by the hair.

“How do you feel about your first porn?” The rough man pulled her to face the camera. Big, pale green eyes surrounded by dark mascara looked out at the camera. Her face was round, slightly cherubic with a hint of baby fat, framed by short black hair streaked with pink. She looked much younger than the woman in the other video.

“I’m excited.” She sounded nervous.

“Oh yeah? We’ll see how you feel in a little bit.” There were a few gruff laughs from off camera. The second man, shorter and a little fatter than his companion, pulled her face towards him.

“This really your first porno? We usually get girls with a little more experience, and you don’t look a day over 16.”

“I’ve had sex with three guys, but this will be the first time I have a threesome.”

“Yeah, you ever been fucked in that cute little ass of yours?”

At this point the camera panned down to show a petite, skinny girl with perky but small tits. She bent over, or more accurately was bent over, revealing a toned ass which the short man slapped.

“No. Well, my second boyfriend tried once, but it hurt too much. We don’t have to do anal though, right? I can suck one of you off while the other has sex with my pussy.”

“Haha, we’ll see you little slut.” The tall man laughed.

Anna was liking the rough handling, but this was a seriously boring start. She skipped forward on the video. It did get rough, a few minutes in the girl was straddling the taller man, and he was pounding his cock into her. The second man had one hand around her throat, cutting off her air, while his right hand alternated between slapping her tits and her face. He was not holding back on these slaps, and her chest was already bright red. Tears were running down her face, leaving mascara tracks all over. Eventually she started turning blue, and started pulling desperately at the man’s hand around her throat while he pulled hard at her nipples. The taller man never once let up on the vicious pounding he was giving her cunt, and as the camera zoomed in on her face you could see real fear in her eyes.
“This is what I’m talking about” Thought Anna, sliding her hand under the thong to rub her soaked cunny directly. The man finally let go of her throat, and she drew a deep breathe, coughing and massaging her bruised neck.

“How do you like porn now, whore?” The short man slapped her face one more time. “C’mon Jack, my turn for her cunt you don’t want to blow too soon.”

Jack lifted her off his cock easily, then stood up while laying her across the arm of the couch.
“So how do you like your first porn now, slut?”

“This is really intense you guys, my pussy is a little sore, and the choking was really scary. Maybe we can go a little easier?” the girl was rubbing her tits tenderly.

“Oh I was just getting your tight little cunt ready for my friend, it wouldn’t be nice for us to start you out on that monster.”

The camera backed out again, taking in the couch with the girl, and the shorter man who was pulling out his cock.

“He was warming you up for 8 inches of cunt destroying fun!” He gleefully said as he lined himself up with her cunt. The girl winced as he started pushing it into, and the camera zoomed in on it. Her pussy was having a hard time stretching to accommodate the large cock, and you could hear her discomforted moans as he forced it deeper. Thinking back to the picture, Anna took out her phone and tried to compare the picture she had to the man in the video.

“Jesus Christ, he is huge. That girl is having trouble taking that guy’s cock, and it’s at least an inch or two shorter. And a lot thinner too!”

Anna started pushing her fingers, one at first and then two, into her pussy. She looked at her phone, thinking how it would feel for such a larger cock to push open what felt like an impossibly tiny hole. When she looked up, the man had finally almost fully into the girl, and the other man was roughly fucking her throat. As the short man started thrusting, he got a little deeper each time, until it looked like he had reached her limit. Each powerful thrust elicited a muffled scream from the poor girl. When she finally got released from her deepthroat duties long enough to breathe she begged for mercy.

“Ow ow ow! It’s too deep, you’re hitting my cervix!” She winced as he slammed into her especially hard, not getting his cock any deeper though. “Fuck, that hurts you asshole!”

She looked back at him angrily, and then before she could do anything he slapped her across the face, hard. At that, Anna’s pussy spasmed a bit in a mini orgasm. Maybe this video would be worthwhile afterall.

“Oh, I’m an asshole, huh? Well I’m getting my fucking cock in you, and if you’re too much of a bitch to take it in your cunt, I guess I’ll have to try another hole.”

The video cut out, to Anna’s severe disappointment. It had reached the 10 minute upload limit for this site, but it looked like they had posted the other half as well. As she opened it, a chat window scared her half to death.

Crabbattle: Someone’s up late.

It was Phill’s handle. He mind was racing, what should she do? Sign off? No, that would make it more awkward, she should just act cool.

Eclair2000: Yeah, couldn’t sleep. Just browsing the internet.

CrabBattle: Oh yeah, ‘browsing’ the internet at 2 am, I get it, sure.

Eclair2000: What? So what are you doing up so late then?

Crabbattle: Masturbating.

Eclair2000: At a sleep over? Where’s Jason?

Crabbattle: Other room, probably doing the same. He definitely liked those pictures of you.

Eclair2000: Well they weren’t meant for him and I didn’t even want Val to send them to you.

Crabbattle: You girls liked what I sent?

Eclair2000: It was certainly a surprise, the girls won’t stop teasing me. I mean, that was photoshopped right? Is that monster real?

Crabbattle: 100% real, just over 9 inches. I pretty proud of it.

Eclair2000: Holy shit. You know I’m a pretty small girl, right? I don’t know if I could handle all that.

Crabbattle: Well, good to know where our date is headed.

“Fuck why did I say that?” Anna thought,” I mean, honestly yeah I’m gonna fuck him, but he didn’t have to know!”

Eclair2000: We’ll see. So what are you looking at?
Anna tried to change the subject.

Crabbattle: Oh no, I was honest about what I was doing. You gotta show first.

Éclair2000: I don’t think so, I don’t want to scare you just yet.

Crabbattle: Ooo, so the goth girl routine is just an act, are you actually kinky? I hoped so, but I don’t think you’ll scare me. Honestly, I’m worried it will be the other way around.

Anna considered it for a moment. She could just send a link to that threesome Steph liked. That probably wouldn’t be too weird. But there was always a competitive part of her, and that part was screaming at her to show this guy what you’re really capable of.

Eclair2000: Ok, don’t say I didn’t warn you.

She sent the link, and started the video, determined to jerk her way through the butterflies in her stomach. The video picked up where it left off, with the man starting to force his cock into her asshole. She started to scream, but the moment her mouth opened, the other man shoved his cock back down her throat. All that came out was a muffled yelp followed by gagging. She tried to push him off, but he pinned her arms to her back.

“Fuck she really is tight. This is hurting my cock a bit.” He was only halfway in and the girl was thrashing around like a trapped animal, trying to free her arms from the tall man’s grasp.

“If I feel you teeth come down just a little, I’ll bash your fucking head in you stupid whore.” The tall man warned.

She stopped fighting as much as the man slowly forced his entire cock into her, all the way to the balls this time. After a minute or two she was just sobbing as the men used her from bother sides, and the man took his cock out of her mouth once she was calm.

“Please… please. It hurts so bad.” Her make up was ruined as she plead to the camera. “You’re going to kill me, please let me go.”

“What you don’t like this, whore?” The tall man pulled her face up to look at the camera. “Don’t like being a little pornstar cunt?”

He spit in her face, and Anna could feel a powerful orgasm building. She was on the edge, watching this pitiful girl get abused and mistreated. She wanted to be her so badly.

At this point, the girl had gone limp, sobbing quietly as the man pounded into her harder and harder.

“How do you like being raped on camera, whore? You said you lived with your parents, right? I bet your daddy would love to see his piece of shit daughter getting fucked in the ass like this.”
The tall man standing over her spit in her face again, then covered her in his cum. The camera then focused on the short man, who had picked up paced and taking long strokes into her ass. He started grunting, and one hand gripped her ass tightly while he balled up a fist and punched her in the ribs hard enough for you to hear her breath get knocked out. He drove himself all the way in and held there for a minute, before pulling a softening cock out of her destroyed hole. As his blood covered cock popped out, the camera focused on her still gaping asshole as rivlets of bloody cum poured out of her.

Seeing the man come drove Anna over the edge. Her legs spasmed and every muscle in her body tensed up as a powerful orgasm washed over her. She did her best to suppress moans as she pictured herself as the girl, covered in cum, curled up and crying in the fetal position.

As she caught her breath, the chat window appeared again.

Crabbattle: Holy Shit.

The video was so intense, Anna had forgotten all about Phill. Coming down from the orgasm, she didn’t even feel embarrassed or worried about his reaction.

Eclair2000: I warned you, didn’t I?

Crabbattle: Yeah, But I was expected some pussy light bondage, S&M BS. That was some crazy stuff. You really masturbated to that?

Eclair2000: Just had one hell of an orgasm, so yeah.

Crabbattle: Well now I really can’t wait for our date. And speaking of one hell of an orgasm, I gotta clean up over here before nick gets back. TTYL

The week at school following their sleepover went quickly for Anna. It was early spring, which meant plenty of studying and review for the finals coming at the end of the school year. This kept her suitably distracted through the school days, though she did find herself thinking of the coming date on Friday with Phill. When Friday morning came she got up early to shower, make sure she was silky smooth from the neck down, and stood in front of her full mirror to finish preparing.

First picking out a very see through lace thong, one of her favorites, she put on a matching black lace bra that accentuated her already considerable bust nicely. She put on dark eyeliner and went heavy with her mascara, something she would previously forgo. To contrast it she did her lips up with a deep red, glossy lipstick. Looking at herself in the mirror, Anna considered her look for a moment.

“Maybe I’ll go a little Lolita with this…” She thought out loud, rummaging through a drawer looking for something.

“Here, perfect.” She pulled out two long red and black ribbons, and after braiding her hair into twin pigtails tied them into bows at the ends. Flipping the pigtails around and donning an innocent look, she play flirted with the mirror childishly. The contrast of sluttish and childish was perfect, she decided.

“Now what to wear?”

Anna’s style had been definitely gothic for the past couple years, but the clothes she wore were generally older and not very showy. Steph would often chide her for wearing clothes from elementary school, but she thought if they still fit, why not? Well, they still fit somewhat, with her expansive chest many of her old shirts were stretched, and wouldn’t cover her flat belly anymore. And the waist on most of her pants had been stretched enough that they would sit lower than her hips, resulting in her usually wearing what amounted to belly shirts and super low rise jeans.

“I think it’s time to wear something new.”

Anna did own plenty of new clothes, after all, she just rarely wore them for various reasons. When she was in 6th grade her mother had given her money to go out and buy all new clothes, to look good in school. As she looked through the drawer, she was reminded why most went unworn. Shopping for yourself was fun, but she really went all out on the goth slut look, and she was never comfortable wearing most of it in public. Searching through fishnet tops, corsets, stockings and miniskirts, Anna was slowly building the courage to pick something out.

“Ok,” Anna breathed out heavily, “I can do this.”

She pulled out a crop top she remembered thinking looked really cute. It was a tiny t-shirt, black with a white skull and crossbones in the center. It had no collar, and would’ve been an tube top if not for the short sleeves that rested halfway down her arms. Pulling it on, she realized while she hadn’t grow upwards in the past two years, she certainly grew outwards. The fabric stretched over her chest, and while it was supposed to rest a little higher than her belly button, now the shirt stopped just short of the bottom of her bra. The overstretching of the the cloth had the added effect of making it considerably see through, with her bra, and cleavage, pretty visible.

Satisfied with her shirt choice, now was the time to find a good bottom. This presented a little more difficulty. She may be very short still, but the past year her hips and bottom had expanded outward into a very womanly shape. As such, a lot of these clothes wouldn’t fit her waist, and unlike her usual ratty jeans and leggings these hadn’t been stretched by regular use. So after trying to squeeze into maybe half a dozen pairs of mini skirts, short shorts and even a pair of leather pants, Anna finally found a black skirt that could still fit.

“I really need to get new clothes.” Anna turned in the mirror, seeing how the skirt looked on her now. It was actually not one of her sluttier skirts, a full 12 inches long which on her 4’10” body would normally be a decent length. That was when it rested low on her hips, however, and in order to work around her filled out hips she had to wear the skirt much higher on her waist than normal, nearly past her belly button. It was actually the fashion these days, but you usually wore a skirt specifically made with that in mind. This was not one of those skirts. The result was that the loose pleated skirt turned into a much tighter one gripping wide hips, and ended mere inches from the bottom of her toned ass. As she spun around in the mirror, the skirt had enough looseness left in it to twirl, easily revealing her ass.

“I’ll have to be careful on stairs I guess.” Anna thought. For shoes she took out a pair of heels she had been waiting for the right occasion to wear. They were black and silver stilettos, done up like sandals and with a steep four and a half inch heel. Satisfied with her look, she grabbed her backpack and headed for the bus stop.

As she walked to the corner to wait for her bus, Anna’s confidence started evaporating. She didn’t live in the busiest part of the city, but she felt like everyone was looking at her. It didn’t help that she did catch a least a couple men undressing her with their eyes on her short walk. She tugged at the skirt, now embarrassed by the amount of skin she was showing, and had a hard time keeping her bra from poking out from under her shirt. She was relieved to see she was the only one waiting for the bus today, usually there were two or three other kids waiting on the corner.

As she waited, an unfamiliar car pulled up to the curb. She didn’t think anything of it at first, but the middle aged man driving started waving her over. She stared at him for awhile, trying to remember who it was or why he would know her. She slowly walked over, still trying to not be obvious about forgetting who this was.

“Hey,” She said in a friendly tone, as if she knew him. Hopefully he would introduce himself or let her know who he was to save her this social embarrassment.

“Hey sexy, how much to party?” The man asked, without taking his eyes out of her tits spilling out of her top.

“Huh? What?” Anna was confused, and didn’t put it all together at first. She realized what he meant as he replied.

“How much to get that sexy little mouth of yours? Or see what you have under that skirt.” He said.

“Oh fuck you!” She was mostly angry at feeling dumb for not knowing what was going on immediately. But she also tugged down her skirt, and rearranged her shirt in indignity.

“Don’t dress like a whore if you’re not putting out like one!” The man shouted, looking indignant as well.

Anna still felt flustered as he drove off, but a little part of her was turned on. She was propositioned on the street! It lit a small fire in her, and she could feel her cunny get warmer. It also brought back some memories, from when he mother was still around more, but those she chose not to think about. A thought for another day perhaps.

The bus pulled up, and she was happy to get off the street. She was dreading facing her classmates like this, but that little fire in her was looking forward to the exposure.

“G’morning Mr. Longo.” She greeted the bus driver, who could barely keep his mouth closed. She could feel his eyes, as well as the eyes of the dozen or so guys on the bus, on her as she looked for her seat. Valerie, who lived just down the block, waved her hand and she joined her friend.

“Holy shit Anna, you go all out for a date!” Valerie leaned back to take in her friend’s appearance.

“You like it?” Anna was trying to pull her skirt lower, but with the tight waist it wouldn’t budge. As it sat she was pretty sure you could see her thong.

“Well, it’s not for me is it? You think Phill is going to?”

“I think so, I think he said he like the ‘goth slut’ look.” Anna said, “I’m not sure about this top though, my stupid bra keeps popping out.”

“Yeah, I see. It certainly is slutty. But what did you expect, that shirt barely fits around your chest. You got your bra popping out the bottom, and your tits coming out the top!”

The bus pulled into PS 103, and the two friends went to their separate classes. The whole school day went by in a breeze for Anna, punctuated by lascivious looks from her male classmates, and a few teachers, and with disgusted glares by the other girls. After the initial embarrassment, Anna actually found herself liking the attention. The hungry looks she got from the guys got her teasing them, ‘accidentally” flashing her ass, or even her thong covered crotch at more than a few of them. Meanwhile, the other girls would gawk at her, and more than a few muttered ‘whore’ or ‘slut’ as she walked by. This just had the effect of making her feel even more horny, like she would work to prove them right.

At one point, her path crossed with Phill’s. He saw her walking down the hall ahead of him, heels clicking loudly on the floor, and skirt bouncing up to tease just the edge of her perky ass with every step. Walking up behind her, he called her name to catch her attention.

“Anna!”

She turned around and went into an immediate blush. He wasn’t supposed to ambush her like this!

“Wow, you look fucking amazing. I feel like an idiot for not dressing up for our date.” Phill looked down at his less than fancy outfit. Dressed in his usual jeans with hoody he blended in with everyone else as much as Anna stood out. He did stand taller than most, puberty making him shoot up to almost six feet tall over the last summer. But whereas Anna had been transformed from little girl to voluptuous woman in one hormone fuel burst, Phill was very clearly still in the throes of puberty. His arms and legs seemed a little too long and skinny for his body, and he was clumsily unsure of what to do with his newly unfamiliar body. His face had gone from rounded with baby fat to a sharply angular, almost gaunt look that promised to grow into a distinguished profile given time. His skin suffered a little from the usual teenage woes, with pimples and blackheads appearing as fast as they could be removed.
“Really? You don’t think this is a little much?” Anna looked down at herself, mirroring Phill, and tugged her skirt down a little more.

“A little much? I’d say you’re barely wearing much as it is!” Phill joked. “I got to get to class, can’t wait to see you after school!”

“Good luck!” Steph shouted to Anna as they part ways at the end of the day. She met her date on the corner opposite the school, waiting for the city bus to take them to the movie theater. The ride over wasn’t half as awkward as Anna imagined it would be. What started with stuttering small talk about similar interests, they both liked video games and chinese food, gave way to some of the most natural conversation either had had with someone. They made dark jokes about the people on the bus, made fun of pedestrians they saw, and in general seemed on the same wavelength all the way to the theater. Anna was so absorbed in conversation she hardly noticed the looks and leers her outfit was drawing, and before long they found themselves sitting in the dark movie theater watching the upcoming trailers. As they sat quietly watching the screen, Anna felt Phill’s hand brush against hers as they put their arms on the same armrest. Slowly, he moved it over her hand until, butterflies in both their stomachs, they finally were holding hands. Anna was happy it was dark, better to hide the embarrassing grin on her face. She might have felt better knowing that Phill was sporting the same look, but he was doubly glad for the darkness hiding the growing bulge in his pants.

As the movie went on, Anna found her mind wandering from what was on the big screen, her thoughts turning once again to that picture on her phone, and the fact that it’s subject was just a couple feet away. Peeling her hand from Phill’s, she casually laid her arm across the armrest to rest her hand on his lap. She surreptitiously petted around, eventually feeling a growing bulge under her hand. Meanwhile, she could feel Phill’s hand creeping up her bare legs, inching closer and closer to her waiting crotch. Looking over at him, Anna bit her lower lip as she unbuttoned his rapidly tightening pants, and slid her hand in to grip his still growing cock. Slowly stroking it, her hand felt positively tiny trying to wrap around it completely. Glancing around to see if anyone was paying attention to them, she reached over to fully undo his pants and pull his cock out to see. The picture she had been obsessing about did nothing to prepare her for seeing such a prodigious member up close. Her earlier fears of its size felt fully justified now, and she was worried again about taking such a large cock.
As Anna was paying attention to his cock, Phill had taken his eyes off the screen to appreciation the scene before him. Anna was bent over the armrest, chewing her lip as she slowly stroked his now fully erect cock. Her too small t shirt had given up, and her tits were spilling out to sit on the armrest with her bra. Looking across her back, he could see her skirt had ridden up to the point of no longer covering anything. Sliding his arm down her back, he reached past the skirt that was now a belt, and grabbed a handful of Anna’s soft behind. He was surprised how full it felt in his hand, considering how small of a girl she was. By now, Anna was pushing back against his hand, and looking up at him hungrily.

With Phill’s hand now even closer to her overheating vagina, and no words exchanged, Anna focused once more on the cock in front of her. There was no way she could take that monster fully into her mouth, but she was desperate to feel it inside her.

“Maybe just the head…” Anna thought, “It’s not like he is expecting me to deepthroat him. For all he knows I’ve never sucked a cock before, so of course it won’t be great.”

Leaning forward more, Anna was now perched on her knees, with her ass and thong visible to any who cared to look. First licking the tip of his cock, she opened her mouth as wide as she could a slide the head into it. Her muscles was burning with the strain almost immediately, cock filling her mouth and pushing the limits of her jaw. She had nearly given up when she felt Phill’s hand move from her ass to her wet cunt. She new he could feel how dripping wet she was through the lacey fabric of her thong. He pulled it aside, and as his fingers finally touched her glistening sex she let out a muffled squeak and got goosebumps all over.

The strain on her jaw was forgotten as his fingers probed her hole, trying to push their way in. When he finally got two of his fingers in she let out a deep moan. It hurt, feeling herself stretch to accomdate his large fingers, but feel impossibly good. Anna immediately started rocking back onto his fingers, taking them deeper and relishing the feeling of her cunt open up for him. Finally she pushed back hard, and felt him slide all the way to the knuckles. Pulling off his cock, she gasped loudly for air.

“What do you say we skip the rest of this movie?” Anna looked seductively into Phill’s eyes. “I have the house all to myself if you want to come home with me.”

Really hope people are enjoying this, always open to comments/suggestions.

Chapter 3: First Timers

For the entirety of the short bus ride to her house, Anna and Phill were completely absorbed into their own little world. They didn’t even notice the stares Anna’s overly revealing outfit got, nor did they worry about being seen as they masturbated each other in the back of the bus. All they saw were each other and all they knew was a desperate desire to fuck.

Anna lived in a three floor condo at the back end of a moderate sized complex. It was hidden away from the street and removed from the other units by a thick firewall. The condo was designed for a small family, but Anna had it all to herself since her mom had moved out a few years ago, a fact she kept carefully hidden from even her best friends. If anyone knew she was living alone they would certainly follow up with questions like why did her mother move out and where was she now, and those were questions she didn’t really want to field at this point in her life.

The two nearly fell through the door as they raced down to Anna’s room in the basement. Anna laid down on her back in the bed, and Phill quickly climbed atop her. Their enthusiasm more than made up for the lack of skill or experience as they made out and felt each other all over. They continued this only for a few minutes, as Anna’s hand had found its way into Phill’s pants, and he was pulling desperating at her bra clasp.

“I’ll get it.” she said, pulling herself up on the bed. Pulling her scrap of a shirt over her head with one hand, she reached back and undid her bra with the other. The bra fell away, revealing her pert young breasts with quarter sized pink nipples. Phill was practically drooling standing at the edge of the bed as her pulled his own shirt off, followed by his pants. As he got his jeans and boxers off, his huge erect cock sprung out, and Anna finally got to see it in all of its 8.5” glory.

“Oh fuck it’s beautiful,” she said, crawling to the edge of the bed to get closer. Wrapping her tiny hand around it she could still only hold a little more than half of its 2.5” girth in one hand. She licked it slowly, from the base all the way to the tip, relishing the feel of each bump and vein on her tongue. Pausing at the top she took a breath and opened her mouth as wide as she could. She was determined to give him at least decent head. She may be a virgin but at least she knew how to suck good cock. Still, he was just too wide, and she could not do much more than hold his head in her mouth and push her tongue against its underside. After a few minutes of trying to get it deeper, she gave up and pulled off his cock with a POP!

“It won’t fit in my mouth,” she said with a frown, “But you can certainly try my pussy.” Anna pulled her thong off and squeezed out of the mini skirt, while Phill awkwardly climbed out of his own pants and pulled off his shirt to match her nakedness. Once his shirt was no longer blocking his view, Phill’s eyes locked to Anna’s bare pussy. Her labia were small, but slightly parted revealing her soft pink inner lips, glistening with lust. She was shaved bare, and felt perfectly smooth as he felt his way down from her waist to her slick vagina.

“You sure, I’m not sure I’ll fit.” He said, still never taking his eyes off her sex as he slid two fingers into her, with some difficulty.
“Uufm, don’t worry I’m sure it will just take some work.” she said, her breathing starting to quicken as his fingers moved inside her. “Just promise you won’t stop until it’s all the way in.” She pulled his hand away from her before laying back and spreading her legs, presenting herself as much as possible to him. He moved toward her, cock in hand, and slid its head across her slit. Both of them moaned in unison and as the tip brushed over her hole Anna rocked her hips into him.

“Mmm, right there. Push it into me.” Anna moaned as he started putting pressure on her tight hole. She started to feel the very tip of his cock push her open, but already it felt too wide for her to take. She bit her lower lip in response to both the amazing feeling of a cock entering her for the first time, and also of the painful stretching she could feel. He pushed a little harder and she could feel her cunt stretch to try to accommodate him. Finally, she felt his head push in and a wave of orgasmic feeling surged through her body. She began pushing up against his cock, and he responded by thrusting down into her abandoning the caution with which he had entered her. Each time he thrust she felt the walls of her cunt tear a little as he forced his cock deeper into her. Soon her moans of pleasure grew deeper as she tried to mask the pain she was in. Anna was determined to take his whole monster cock, no matter the pain.

“How far in are you?” Anna said, daring to hope she was nearing her goal.

Leaning back and making one more strong push at her, he looked down at his cock. “I don’t know, a little more than halfway I think. Are you ok, you look like you’re in pain.”

“I’m fine, I just want to make you feel good. Don’t worry about hurting me, you saw that porn I sent you, right? I want you to fuck me as hard as you want.” Just talking about it made Anna forget the pain and discomfort, she just wanted to feel herself all around his cock. Not questioning her invitation, Phill starting fucking her again, harder than before. He was pulling his cock nearly all the way out, so that she made a pleading little moan, then slammed it into her. After just a few thrusts like these Anna was letting out little grunts of discomfort and she felt her insides get pulverized. By now he was pounding furiously into her, completely taken by the animal urge to get his cock in her. Finally, Phill felt his cock slam up against something hard, and Anna let out a little shriek and clutched at her stomach. Despite making no more progress he thrust hard into, each time she felt a gut wrenching pain deep in her abdomen. She tried to bring her knees together and curl into the fetal position after the sixth or seventh hit, but just succeeded in squirming around in pain. This did bring him out of his frenzy however, and he looked down concerned.

“Oh shit, sorry! Are you ok?”

“I’m fine,” Anna said threw tears,” I told you can use my body how you like. You’re just hitting my cervix I think, and I don’t think you can go any deeper.” Anna reached down to feel her cunt. She could feel his cock, squeezed by her lips, and was amazed at how wide it was stretching her. She brought her fingers back to see they were covered in blood. “Holy shit you made me bleed.”

“Well, yeah isn’t that supposed to happen the first time?” he replied with a little confusion.

“Only if I had a hymen, I broke that years ago. No I think you just tore me up a lot. How deep can you get anyway?”

“It looks like seven inches maybe, almost all the way. But I don’t think I got any deeper once I hit your cervix. I think you’re just too small for me.” He answered, slowly moving his cock in and out by an inch.

“Well, yeah, but it looks like it’s not going to happen.” Phill said, still playing with her bruised cunny.

Thinking back to the porn she showed him, Anna made a decision.
“God this a stupid idea.” Anna thought to herself, “I really can’t be this dumb, right?”

What she said, however was, “Well, sure you can’t fit it all in my cunt, but I bet I could take it all up my ass.”

It took Phill a moment to recover from the shock. “What? Are you serious? And don’t we need lube or something?”

“I want to make you feel good. And I think your cock has enough of my cunt juice and blood to count as lube. Besides, maybe it’ll feel better this way.” Anna looked at him earnestly, “But seriously, I want you to fuck me as hard as that video, don’t worry about how I feel, ok? Promise?”
“God you’re a fucked up slut, you know that?” Phill said, finally finding his role in her fantasy.

“Mmm, yes I am. I’m your fucked up slut and you can fuck me up anyway you want.” She said, biting her lip again. As he pulled out of her, she was amazed by how empty her cunt now felt. It felt like her pussy was hanging open, and in reality it was gaped open slightly. She marveled once again at his bloody cock, before turning over and getting on all fours. Soon she felt his cock once again pushing for entry, this time to her much tighter butthole. It was much tighter in fact, and at first neither of them were sure he would be able to get inside at all. But eventually, between Phill pushing forward, and Anna pushing back and making sure his cock didn’t slip down into her ruined cunt, the massive cock started to open her up. Anna winced and tried to hold back a scream as her tight muscle was forced to open. This was much worse than having her pussy stretched, where that had been pleasure mixed with pain this was just sharp, burning pain.

“Oh fuck that’s tight.” Phill moaned in ecstasy as his cock steadily pushed deeper into her. Anna bit down on her pillow and tried masturbating, hoping to distract herself from the horrible pain of her virgin asshole being torn open. She tried imagining what it looked like for him, his giant cock disappearing into her small body. She focused on how she was being used and abused for someone else’s pleasure, a fantasy she often had. But nothing could distract her from the pain, and soon she was screaming into her pillow.

Although he was enjoying using her like this, Phill was still aware of how much this must hurt. He was determined not to lose control again, and was trying his best to balance not hurting her with his own desire to fuck her. He was slowly getting deeper, with his slow and soft thrusts, and finally after what felt like hours Anna felt his hips press up against her ass. He reached forward and grabbed a hold of her hair, pulling her red face off the pillow as he used her to get leverage enough to thrust the final half inch into her strained asshole. She looked back at him through bloodshot, tearing eyes.

“Now I’m going to fuck you like the piece of shit sex doll you are.” He snarled at her, before spitting in her face. Feeling his hot, sticky spit across her face gave Anna’s lust the push to cut through the searing pain of her asshole being ripped up by a cock and had her feeling close to orgasm finally. She furiously rubbed her clit as Phill pounded roughly into her, each thrust pushing deeply into her stomach. But it was too much for her, and she soon gave up as the pain of her torn ring combined with a deeper pain in her stomach to overwhelm her senses. She tried pushing him away with weak arms as she sobbed into the pillow. But Phill was too into the feeling of her small body squeezing his cock to stop now, and slapped her arms aside as he felt his orgasm build up. Grabbing her hair and pulling her face off the pillow, he buried his cock as deeply as he could and felt stream after stream of his cum shoot deep inside her colon. Grunting and releasing her head, he collapsed onto her, pinning her to the bed.

Anna was still quietly crying into her pillow as he lay on top of her. As she tried to process everything, she wished she could feel his cum inside her. She always wanted to know what it felt like, to be filled with a man’s cum. She thought it would be hot, feeling dirty and used inside. While she did feel used, unfortunately all she could feel inside was a deep throbbing pain. She could feel every little movement of his rapidly softening cock as it pulled at the little cuts she had inside.

“Oh god, I’m so sorry.” Phill had finally seemed to come to his senses. “Are you ok?”

Pulling his cock out of her, Phill pushed himself off of her and moved to sit across from her on the bed. Feebley, Anna started to curl into a fetal position. Not only did her ass burn, but deep in her stomach she still had cramps from her upper colon being invaded. But hearing him apologize worried Anna.
“He shouldn’t feel bad for me!” Anna thought, “This is what I’m hear for.”

She wanted to tell him, but knew she couldn’t hold herself together well enough to talk without bursting into tears. Instead, she looked over at him through the corner of her eye. He was sitting, legs half crossed, with a concerned look on his face. Draped across his leg was his cock, still a sizable 6 inches or so, covered in a mess of blood, cum, and probably shit. Doing her best to ignore the pain, Anna crawled forward and took the head of his cock into her mouth. She was immediately assaulted by many awful tastes. Anna had sucked some nasty cocks in her young life, but nothing quite like this mixture. Foremost was the irony tang of her own blood, which coated the cock from base to tip. But under that she tasted the familiar bitter saltiness that was most definitely his cum. Finally, there was the deeply bitter taste of her own ass, a taste so vile she gagged and barely held back her vomit with that first taste.

“Oh fuck.” Phill was in shock again, looking down as Anna took the whole of his cock into her mouth, and she worked hard to clean every inch of it. Her face was a mess. Her mascara, over applied as it was, was covering her cheeks. Her eyes were bloodshot from crying, and spit dripped from her chin. Her lips were red from smudged lipstick, but also her own blood, with a slight brown tinge from the shit she cleaned off his cock. She licked her lips clean and looked up at him.

“You see? My body is yours to use and abuse. I’m your sex slave!” Anna said, putting genuine cheer into it in spite of her condition.

Reaching down to stroke her cheek, Phill drew her face to his and kissed her passionately on the lips.
“And what a perfect little sex slave you are.” He softly kissed her forhead, and Anna felt a warm contentedness fill her heart as she curled up in his lap.